Biomaterial Database

One-pot approach to 2,3-disubstituted-2,3-dihydro-4-quinolones from 2-alkynylbenzamides. 2011

Noriko Okamoto, and Kei Takeda, and Minoru Ishikura, and Reiko Yanada

Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima 737-0112, Japan.

Concise and efficient syntheses of various trans-2,3-disubstituted-2,3-dihydro-4-quinolones have been achieved via tandem Hofmann-type rearrangement of 2-alkynylbenzamides, nucleophilic addition of alcohols to the isocyanate intermediates, intermolecular [2+2]-cycloaddition with carbon-carbon triple bonds and aldehydes, and intramolecular aminocyclization of nitrogen of carbamates to the α,β-unsaturated ketones.

UI	MeSH Term	Description	Entries
D007659	Ketones	Organic compounds containing a carbonyl group	Ketone
D002219	Carbamates	Derivatives of carbamic acid, H2NC(	Carbamate,Aminoformic Acids,Carbamic Acids,Acids, Aminoformic,Acids, Carbamic
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D000475	Alkenes	Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408)	Alkene,Olefin,Olefins,Pentene,Pentenes
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D042462	4-Quinolones	QUINOLONES containing a 4-oxo (a carbonyl in the para position to the nitrogen). They inhibit the A subunit of DNA GYRASE and are used as antimicrobials. Second generation 4-quinolones are also substituted with a 1-piperazinyl group at the 7-position and a fluorine at the 6-position.	4-Oxoquinoline,4-Quinolinone,4-Quinolone,4-Oxoquinolines,4-Quinolinones,4 Oxoquinoline,4 Oxoquinolines,4 Quinolinone,4 Quinolinones,4 Quinolone,4 Quinolones